


testing you out

by Madfalldyn



Series: Commissions [8]
Category: Kill la Kill (Anime & Manga)
Genre: Age Difference, Alternate Universe, F/M, Incest Play, Mommy Kink, Nipple Licking, Nipple Play, Vaginal Fingering, Vaginal Sex, commission
Language: English
Status: Completed
Published: 2020-08-05
Updated: 2020-08-05
Packaged: 2021-03-06 07:41:20
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,309
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25719742
Author URL: https://archiveofourown.org/users/Madfalldyn/pseuds/Madfalldyn
Summary: You were bold enough to ask out the Kiryuin sisters, but their mother has to make sure you're worthy of her daughters, first.
Relationships: Kiryuuin Ragyo/Reader
Series: Commissions [8]
Series URL: https://archiveofourown.org/series/1845484
Kudos: 27





	testing you out

**Author's Note:**

> An anonymous commission, taking place in an AU where Ragyo is not evil, and is instead a doting mother.

Like most of your classmates, you’ve had your eyes on the Kiryuin sisters for most of the school year. Both Satsuki and Ryuko are stunningly beautiful, even if their personalities have little in common. Ryuko is rough and tumble, whereas Satsuki is refined to an extreme degree. They’re each popular, in their own ways, but both are also intimidating. Most aren’t bold (or perhaps, stupid) enough to make a move on them, and while you’re not quite sure what gives you the courage, you ask them out.

Not one of them, but both of them. At the same time. Of course, they’re taken aback. Satsuki glares, while Ryuko outright curses you, but it would seem they’re intrigued, if perhaps a little impressed. Shockingly enough, they agree, but it’s their condition that really throws you for a loop. You have to meet their mother, and earn her approval, before you can date the two of them.

Apparently, this is a general rule for the sisters. Anyone who tries to court either of them would have to be vetted by Ragyo Kiryuin, so that she could ensure any suitor was worthy of her lovely daughters. The Kiryuin family is powerful, and many would want to marry into it just for the wealth and prestige. Of course, Ragyo must be very careful with her daughters. Perhaps many of your fellow students knew this. Perhaps it wasn’t just Ryuko’s attitude, or Satsuki’s cold demeanor, that would drive them off.

Perhaps if you had heard those rumors, about how easily Ragyo would chew up and spit out any potential suitors, or of how their mother was a real battleaxe of a woman, running an entire conglomerate on top of raising two lovely daughters, you might have reconsidered being so bold. It’s too late now, and you’re stubborn enough to go through with this either way. The Kiryuins gave you a date and a time, and told you to be sure to arrive punctually. It’s hard not to be nervous, as the days pass by and the time grows nearer and nearer.

Many of your classmates congratulate you, patting you on the back, and seeming highly impressed that you actually went through with this. Most others, however, treat you like a dead man walking. They’re sure you’ll never be seen around school again, once Ragyo is through with you. It’s hard not to be nervous when some of your fellow students already assume you’ll be dead within the week.

Ryuko and Satsuki both seem fairly calm about it all. They don’t really treat you any differently, even with a potential date on the horizon, and that is perhaps what worries you the most. They seem absolutely confident that, in spite of the fact that they agreed to this date, they don’t see much chance of it actually happening. Whatever else your classmates do or say, the sister’s calm confidence is what truly terrifies you. If even half of the rumors about Ragyo are true, you might be in for a hell of a night.

~X~

Avoiding it won’t do you any good, however. As the day finally arrives, you do your best to go about school as normal. It’s hard to focus, sure, and more and more of your peers have shifted into the camp that treats you as if you’ve already died. It’s all you can do to tell yourself these are just the idle rumors birthed from the overactive imaginations of young adults. Sure, Ragyo is probably somewhat intense, if she’s the head of such a wealthy and powerful family, but it’s not like she can be  _ that _ bad. Right?

Suffering through school, you find the day dragging by more and more. You wish it would just go by quickly, if tonight’s meeting is really going to be this bad, you’d prefer to just go ahead and face the music already. Instead, you have to deal with the way everyone looks at you, whispering among themselves as you walk past. Even some of the faculty seems to be in on things, and you’re shocked to find the rumors would spread that far.

Eventually, however, the day does come to an end. You do your best to look cool, calm, and collected, as you head for the Kiryuin estate. Strangely enough, both Ryuko and Satsuki seem to be avoiding going home. With Satsuki, that’s no surprise. The student council president is heavily involved in many clubs, and will be remaining at school for reasons relating to club business. Ryuko told you it was none of your business what she did, and to buzz off, but you’re pretty sure she’s hanging out with Mako. 

Honestly, they wouldn’t have been very reassuring either way. It likely would have been awkward having them around while their mother decided if you were worthy to date them, so you’re not exactly worried that you’re headed to their house alone. Though, as you get closer and closer, you begin to realize just how much “House” doesn’t cut it. The estate is massive, with a mansion that you could hardly even imagine dominating it. 

The staff all seem to be filled in on what’s happening, greeting you professionally and leading you where you need to go. Soon enough, you’ve been guided and shuttled to the office of Ragyo Kiryuin. More accurately, you’re standing just outside of it, with ornate double doors standing between you and the woman you’ve heard so many rumors about. Your heart is pounding in your chest, as you slowly reach up, wondering if you should simply open the door, since you’re expected, or knock. It’s a simple choice, and it should be no matter, but you quickly stumble over the decision. Opening the door shows confidence, but knocking would be respectful and polite. What would Ragyo prefer? Despite all the rumors, you know next to nothing about her, with no hints as to what might best win her over.

“Well?” an imposing voice eventually rings out, from the other side of the door. The word speaks volumes, somehow managing to be both inviting and teasing. “Are you going to come in, or just stand out there worrying?”

“Ah… I…” you start, stammering. This is one hell of a first impression, isn’t it?

The doors swing open, and the woman standing on the other side is unspeakable. Ryuko and Satsuki are both attractive, and it’s obvious where they get it from. Ragyo is enticing, absolutely stunning to look upon, and you catch yourself looking her up and down. She’s got an incredible figure, complementing her exquisite face perfectly. If this is the future you have to look forward to with Ryuko or Satsuki, you hope you can survive Ragyo’s tests.

“Oh, my. Well, you’re a bit more handsome than I expected,” Ragyo says, sizing you up. You feel like a lamb, led to a lion for the slaughter. She has the eyes of a predator, seeing right through you, stripping you down easily. “But looks aren’t everything, hm?”

“N-no, ma’am,” you answer, immediately.

“Ah, so you do have some manners. Excellent, I was worried with how you simply waited outside my doors,” Ragyo says, chuckling a bit. “Perhaps you’re not entirely hopeless.”

“You wanted to see me, yes?” you ask, deciding not to mention all the rumors you’ve heard.

“Why, of course. You are courting my dear, lovely daughters, are you not?” Ragyo explains, “Both of them at once, from what I hear. Forgive me for assuming you’d be a bit more… bold? Of course, it’s natural any boldness you might have felt at school, around your peers, would shatter completely in my presence.”

“I just… didn’t really know what to expect,” you say, a bit sheepish.

“Tsk, is that right? I bet your head was filled with all sorts of nasty rumors, hm?” Ragyo says, reaching a hand out, and gripping your shoulder. Even through your jacket, you can feel her nails digging in. “I’m not half as bad as all that, you know.”

She smiles, but somehow, that doesn’t make her any less terrifying. Even half as bad as what you’ve heard would be pretty scary, but you’re in way too deep to turn back now. You’re sure things won’t be as bad as everyone thinks, anyway. So far, Ragyo has been nothing but pleasant. Sure, she’s intimidating, but that’s to be expected.

“Sorry, I shouldn’t let baseless rumors get to me,” you say, reaching a hand out. You may not have had the best of first impressions, but you’ll do your best to make up for that now. 

“They’re not  _ entirely _ baseless, but I appreciate the sentiment,” Ragyo replies, shaking your hand. It’s a bit awkward, with her still gripping your shoulder, but you’re not about to say anything about it. “Really, I just love my daughters, and will do whatever it takes to make sure they’re safe. So, you’ve got your eyes on them, hm?”

“I do, yes,” you admit, trying not to hesitate, or stammer. “They’re both quite beautiful, and it’s no wonder, considering their mother.”

“Oh, hush! Flattery is nice, but empty. Still, I do appreciate the compliment,” Ragyo says, chuckling softly. “I’ll have you know, anyone that seeks to date either of my daughters must be approved by me. I’m  _ very _ protective, and want to make sure they have only the best. Some rude boy seeking only to take advantage of them simply wouldn’t do, and I couldn’t bear to see either of them hurt.”

“Of course, ma’am. I’d never do anything li-” you start, thinking you’re already on to the basic assurances. Ragyo shifts suddenly, however, sliding a finger over your lips, silencing you.

“Now, now. Anyone can say such empty words, you know,” she says, shaking her head. “They really don’t mean much, in the grand scheme of things, do they? No, I need you to prove yourself to me.”

“Prove myself?” you ask, confused.

“Yes, I need you to show me that you know how to treat a lady. I need you to court me as you would my daughters,” Ragyo explains, “To take me out for an evening, and do everything you can to show you’re a man worthy of the Kiryuin family, and not some boy biting off more than he can chew.”

“You want me to take you out on a date?” you ask, incredulous.

“I’m not going to repeat myself, young man,” Ragyo states, simply. There’s so much behind that statement, however, that you wouldn’t dare push.

“Sorry, right. Of course. Would tonight be okay?” you ask, not entirely sure of when Ragyo had in mind.

“Oh, eager, aren’t we?” Ragyo teases, “Not even trying to buy yourself some time? Well, I must admit I set aside enough time just in case. I’m yours for the evening, so prove to me that you deserve to date my daughters. Keep in mind, however, that disappointing me is a terrible idea.”

“I don’t think I’d be able to forget that even if I tried,” you say, shaking your head. Ragyo is so intimidating, but you think you’ve at least made it through the first stage of… whatever the hell this is. If you just make this date as great as possible, you just might be able to make it through this. Not only would you prove yourself to your classmates, but you’d get Ragyo’s approval to date her daughters. 

“Well, I won’t burden you  _ too _ much, since I sprang this on you. I’ll pick where we go, alright?” Ragyo says, already heading for the mansion’s exit. You’re left to follow after her, doing your best to keep up with her confident pace.

~X~

You’re not at all surprised when the car stops in front of a restaurant you’ve only ever heard of, and knew better than to even consider being able to afford. Sharing the back seat with Ragyo was not as unpleasant as you’d thought it might be. She is at least lovely to look upon, and you stole more than a few glances at her. It might have been risky, but you don’t think she noticed.

Her figure may be lovely, but the conversation she made was less so. Every discussion seemed to lead to something, to be trying to root out some facet of your personality, or even your dreams. Ragyo is certainly a skilled conversationalist, leaving you on your toes for the entire trip. You’d hate to work beneath her, or to be negotiating some sort of business deal with her. 

Most of her questions touched on things you’d hardly even thought about, like what you would do after school, what kind of career you wanted. It would seem she is incredibly thorough, and you hope you didn’t disappoint. At the very least, she hasn’t called the date off yet. 

You open your door, getting out of the luxurious vehicle, and walking around behind, to the other side. You open Ragyo’s door for her, holding out a hand so that you can pull her up and out of her seat. Of course, she doesn’t need any sort of help, but you want to be as over-the-top polite as possible.

“My, my, chivalry isn’t dead, hm?” Ragyo teases, causing you to blush. Even trying to be a gentleman, she makes you feel like you’re in way over your head. “Thank you, young man.”

You walk into the restaurant together, and are shocked when Ragyo simply… walks to a table, and has a seat. You’ve never seen anything like it before, expecting to have to wait for the hostess to seat you. Naturally, Ragyo has her fame and power, and you’re reminded of this as you notice a server approaching her immediately. Whatever else was going on this evening, it’s all been put on hold for Ragyo. 

You’re eager to eat, realizing that beneath all your nerves and worries, you actually are quite hungry. Maybe you can finally relax for a bit here, and calm yourself. As long as Ragyo stops grilling you, this might actually be an enjoyable meal.

It shouldn’t be any sort of surprise, then, that Ragyo interrogates you all through dinner as well.

~X~

Once you’ve suffered through dinner, the two of you get back in the car, now heading back for the estate. You continue to hope you haven’t bumbled things too badly, yet. Ragyo doesn’t seem like the type to keep you in the dark, or waste her time, and you’re sure if she gave up on you she’d tell you and put an end to all this. 

It seems she’s finally running out of questions, opting instead to make small talk. Without the interrogation, Ragyo is actually pretty pleasant to talk to. She’s witty, and quick on her feet, but not without a sense of humor. You’ve made several jokes, and she seemed to like them all, even placing her hand on your leg as she laughed once or twice.

It’s getting harder and harder not to stare at her, as the night goes on. Her intimidating air hasn’t faded, or anything, but you’re growing a bit more used to it. Comfortable with it, even. You still feel like you’re out of your element, like she’s sizing you up with every moment, but you’re not as worried as you were at first.    
The fact that you’re able to joke with her at all speaks volumes, and she seems pleased with how comfortable you’ve gotten. Comfort comes with risks, of course. Her stunning beauty that was tempered by your fear becomes more and more difficult to ignore. She really is gorgeous, and dresses to suit her features perfectly. You get so lost in her, you hardly notice that she is slowly moving her hand up your leg.

It’s not until she’s squeezing your thigh, gently, her nails pressing into you, that you notice what she’s doing. You don’t cry out, or anything that dramatic, but a light gasp is enough to tip her off.

“Oh, is that too much for you?” she asks, chuckling. “I’m sure you’re rather… inexperienced, hm?”

“M-ma’am?” you ask, playing dumb. Isn’t she testing you to see if you’re worthy of her daughters? Why would she be… touching you? As much as this confuses you, it’s exciting, too. You feel yourself growing hard, finding it impossible not to give into the arousal that’s been threatening to come to a head all evening. Ragyo is simply too gorgeous, this little push is more than enough to ruin you.

“Ah, of course. I’m getting ahead of myself, we should really wait until we’re back, shouldn’t we?” Ragyo says, as if whatever is going on is perfectly normal.

“Wait for what, exactly?” you ask, and Ragyo seems shocked.

“What? Did you think a date would be the end of it?” She says, as if this is all some natural, expected ritual. “You have to prove yourself in bed, too.”

Finally, she pulls her hand back, but it doesn’t do much to comfort you. Whatever confidence you had built up before shatters now, in the face of this unexpected turn.

~X~

It’s difficult to calm down, especially as Ragyo leads you to her room. You’re basically catatonic, as she seats you on her bed. She seems excited, eager to get started, but you are still in shock. She’s stunning, and you definitely want her, it simply feels a bit weird to have the woman you might someday call mother-in-law testing you out like some new product.

“Relax, dear,” Ragyo says, noticing how you’re feeling. “You’re doing great so far, and someday you might even be lucky enough to call me ‘mother,’ so there’s no need to worry so much. Besides, it’s not as if I didn’t notice you stealing glances at me all night.”

You don’t answer, at least not verbally. The way your cheeks begin to flush, however, gives you away. You were definitely checking Ragyo out, definitely thinking about what a night with her might be like. But it wasn’t supposed to happen! It was nothing more than idle fantasy. 

“Oh, dear. Did  _ Mommy _ make you blush?” Ragyo says, and you gasp. “You like that, don’t you?”

“Y-yes,” you manage to stammer out, but Ragyo only shakes her head.

“Is that any way to answer me?” she asks, “I could be your mother someday, you know.”

“Yes, Mommy,” you correct yourself, and she sighs happily. 

“Ah, I do enjoy the sound of that,” Ragyo says, moving so that she’s standing right in front of you. She reaches down, lifting your chin so that you have to look at her. “Show Mommy why you deserve to date my daughters, okay? I’d  _ love _ to add you to my family, especially if you can make me happy.”

She shrugs out of her dress, letting it fall off of her shoulders. She turns, slowly, letting the fabric slide down her body, revealing more and more of her stunning body. You’re surprised to see scars, but they somehow only add to her enchanting beauty. Before you can stop yourself, you’re standing, approaching her.

You let instinct take over, reaching up to grab at the breasts you’ve been eyeing for most of the night. They feel even better than you’d imagined, soft, yet firm, and Ragyo seems pleased you’d go right for them.

“Bold, aren’t you?” she says, chuckling. Spurred on, you guide your fingers to her nipples, slowly teasing at them, working them until they harden under your touch. “Ah, that’s such a good boy. Making Mommy so proud.”

“I’m glad to hear it,” you respond, shocked at how natural this feels. Ragyo is acting as if she’s your mother, all while you work to pleasure her, and yet it feels natural? It’s so weird, completely bizarre, but you’re not about to question it.

“You can suck on them, you know,” Ragyo says, and you know it’s more of a command than anything else. “It’s okay, I don’t mind guiding you through all this. You’re still so young, after all.”

You lean in, touching your lips to one of her nipples. She inhales, sharply, as you take her into your mouth, running your tongue over her. You begin to suck, gently, all while rolling your tongue over her erect nipple, and Ragyo reaches up, stroking the back of your head. 

“That’s good, that’s so good. I’m rooting for you, you know. If you marry one of my daughters, well, then you’d  _ really _ be my son,” Ragyo says, and you’re not sure why that adds to your excitement. Tonight is shaping up to be a very weird night for you full of thoughts you wouldn’t have expected.

She moans softly, enjoying the feeling of your mouth, but after a moment, she pulls you back. Before you can question it, she’s pulling you into a sloppy kiss, shoving her tongue into your mouth. It takes you a moment to catch up, but soon, the two of you are locked in a passionate kiss. You explore her body as you kiss, stroking her back, feeling the shape of her scars, and marveling at how much firmer that skin is. She doesn’t mind the attention, but you move on before long. 

Feeling especially bold, you drift between her legs, stroking her cunt experimentally. Ragyo breaks the kiss, then, as she spreads her legs.

“Mm, that’s a good boy. You know just what Mommy wants, don’t you?” Ragyo says, placing her hand over yours. She begins to guide you, coaxing you into touching her, and eventually into fingering her. Your touch is enough to make her whimper, and moan, even if she is the one guiding you. Hearing such lewd noises from Ragyo is enough to drive you mad, and you find your arousal building by the second. 

Eventually, she pulls back from you completely. She takes a seat on the bed, spreading her legs, and motions you in closer. You follow after her, starting to climb in after her, but she shakes her head.

“No, no, I need you to wait a little longer, okay?” Ragyo says, “Kneel between my legs.”

You know what she has in mind without being told. She wants you to eat her out, and while you’ve only read about such a thing, she’ll likely be guiding you through this as well. At this point, you wonder if she’s not testing your potential more than any real skill or talent. Perhaps if you show her that you have the aptitude to learn, that will be enough?

Eager to get to work, you kneel. You don’t hesitate, burying your face between her legs. You understand the basic premise, so you press your tongue into her folds, tasting her arousal as you explore her body with your tongue. Ragyo moans, and reaches down, guiding you. She pushes you against her, driving you in even deeper. 

“That’s a good boy, so eager to please,” Ragyo murmurs, “You’re doing such a good job.”

With her words of encouragement ringing in your ears, you redouble your efforts. You begin tracing shapes within her, focusing wherever seems to get the most reaction. Before long, she’s crying out, whimpering, and you think you might actually be able to finish her. You don’t dare slow down, or stop, you simply have to keep at it. You push her, further and further, until she is trembling. Finally, she moans, a desperate breathy moan, and you know you’ve done it. 

She pulls you up, almost before her orgasm is through, pulling you onto her. She guides you, so quickly you hardly realize what’s happening, unzipping your pants and freeing your cock, then guiding it to her cunt. 

“Such a good boy, Mommy has to give you your reward, doesn’t she?” Ragyo murmurs, and you wonder if she even remembers the point of all this. You aren’t sure if you care, truthfully, especially as she pulls you in. You sink into her, your cock surrounded by the warmth of her cunt, practically sucking you into her. 

After waiting for so long, pleasuring her so much, you simply can’t stand the thought of holding back. Ragyo whimpers, as you begin fucking her frantically, desperately. You can’t hold back, there’s just no way, and she seems to be equally lost in pleasure. All thoughts of passing her test vanish, and all you can think of is how badly you want Ragyo, how incredible this feels. As you fuck her, she begins working her hips from side to side, using her experience and skill to drive you mad.

Ultimately, you don’t stand a chance. Ragyo is far too much for you to handle, and no matter how much you want to make this last, there’s just no way. Before long, you are groaning, straining just to hold out for one second longer. Once you finally reach your limit, you collapse onto her, pushing into her one last time. You cry out as you come, your seed spilling into Ragyo.

“That’s right, come inside Mommy,” she says, urging you on. “You’re such a good boy!”

You can’t believe things have led to this, that you came here to see if you were worthy to date Ryuko and Satsuki, and instead, ended up fucking their mom. What would they say if they knew? Wouldn’t they think all of this was weird? Perhaps the weirdest part of it all is that you wouldn’t entirely mind if Ragyo wasn’t done testing you.

“Ah, that was great,” Ragyo says, snapping you out of your thoughts. “I’d definitely like you to be part of my family.”

“So… I pass?” you ask, hesitantly.

“Mm, you haven’t failed, at least. My daughters deserve only the best, however,” Ragyo answers. “I think I’ll have to test you a couple more times. Just to be sure.”

You really aren’t sure if you’re relieved, or worried.

**Author's Note:**

> If you're interested in my writing, check out my Twitter for updates and information!  
> https://twitter.com/Madfalldyn


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